GB1050740A - - Google Patents
Info
- Publication number
- GB1050740A GB1050740A GB1050740DA GB1050740A GB 1050740 A GB1050740 A GB 1050740A GB 1050740D A GB1050740D A GB 1050740DA GB 1050740 A GB1050740 A GB 1050740A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- acid
- radical
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,050,740. Indole derivatives. MERCK & CO. Inc. Jan. 29, 1964 [Feb. 1, 1963], No. 2071/66. Divided out of 1,050.728. Heading C2C. Compounds of the Formula I, wherein R 1 is an aryl, heteroaryl or substituted aryl or heteroaryl group, R 2 is a hydrogen atom or a C 1-5 alkyl, C 2-5 alkenyl, aryl, aralkyl, alkaryl or substituted alkyl or aryl radical, R 3 is hydrogen or a C 1-5 alkyl or C 2-5 alkenyl radical and R 5 is a hydrogen or halogen atom or a C 1-5 alkyl, C 1-5 alkoxy, haloalkyl, nitro, amino, substituted amino, cyano, aminomethyl, alkyl-substituted aminomethyl, mercapto, dialkylsulphamoyl or benzylmercapto radical and R x is an alkyl, aralkyl, alkonyl or cycloalkyl radical, are prepared by heating a compound of the Formula II with a compound of the formula R x OH in the presence of an acid catalyst and N-acylating the product with an acylating agent derived from an acid of the formula R 1 COOH. Alternatively the starting material II may be refluxed with acid in a non-alcoholic medium to give the free acid of I, which is then esterified with an alcohol R x OH and acid and N-acylated with an acylating agent derived from R 1 COOH. The exemplified product is methyl α-(1-pchlorobenzoyl - 2 - methyl - 5 - methoxy - 3 - indolyl)-acetate. Indolenins of Formula II are made by adding a dilute acid solution of a p-R 5 -benzenediazonium salt to an alcoholic caustic soda solution of a compound of the formula wherein R z is an alkyl radical, refluxing the resulting hydrazone with alcoholic ZnCl 2 to form the di-ester of a 2-carboxy-indolenin-3-acetic acid, hydrolysing to give the free acid and heating on a steam bath to remove the 2-carboxy group.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25564263A | 1963-02-01 | 1963-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1050740A true GB1050740A (en) |
Family
ID=22969254
Family Applications (13)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1050728D Active GB1050728A (en) | 1963-02-01 | ||
| GB1050736D Active GB1050736A (en) | 1963-02-01 | ||
| GB1050729D Active GB1050729A (en) | 1963-02-01 | ||
| GB1050733D Active GB1050733A (en) | 1963-02-01 | ||
| GB1050740D Active GB1050740A (en) | 1963-02-01 | ||
| GB1050735D Active GB1050735A (en) | 1963-02-01 | ||
| GB1050734D Active GB1050734A (en) | 1963-02-01 | ||
| GB1050732D Active GB1050732A (en) | 1963-02-01 | ||
| GB1050737D Active GB1050737A (en) | 1963-02-01 | ||
| GB1050739D Active GB1050739A (en) | 1963-02-01 | ||
| GB1050731D Active GB1050731A (en) | 1963-02-01 | ||
| GB1050730D Active GB1050730A (en) | 1963-02-01 | ||
| GB1050738D Active GB1050738A (en) | 1963-02-01 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1050728D Active GB1050728A (en) | 1963-02-01 | ||
| GB1050736D Active GB1050736A (en) | 1963-02-01 | ||
| GB1050729D Active GB1050729A (en) | 1963-02-01 | ||
| GB1050733D Active GB1050733A (en) | 1963-02-01 |
Family Applications After (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1050735D Active GB1050735A (en) | 1963-02-01 | ||
| GB1050734D Active GB1050734A (en) | 1963-02-01 | ||
| GB1050732D Active GB1050732A (en) | 1963-02-01 | ||
| GB1050737D Active GB1050737A (en) | 1963-02-01 | ||
| GB1050739D Active GB1050739A (en) | 1963-02-01 | ||
| GB1050731D Active GB1050731A (en) | 1963-02-01 | ||
| GB1050730D Active GB1050730A (en) | 1963-02-01 | ||
| GB1050738D Active GB1050738A (en) | 1963-02-01 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT277992B (en) |
| BE (1) | BE643268A (en) |
| BR (1) | BR6456479D0 (en) |
| CH (16) | CH457435A (en) |
| DE (16) | DE1695492A1 (en) |
| DK (11) | DK109334C (en) |
| FI (9) | FI46955C (en) |
| FR (1) | FR1559559A (en) |
| GB (13) | GB1050738A (en) |
| NL (1) | NL6400813A (en) |
| SE (12) | SE302463B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU163233B (en) * | 1970-07-31 | 1973-07-28 | ||
| DE58902127D1 (en) * | 1988-06-21 | 1992-10-01 | Rauter Vita Zahnfabrik | DISPERSED CERAMICS. |
| GB9518994D0 (en) * | 1995-09-16 | 1995-11-15 | Agrevo Uk Ltd | Fungicides |
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0
- GB GB1050728D patent/GB1050728A/en active Active
- GB GB1050736D patent/GB1050736A/en active Active
- GB GB1050729D patent/GB1050729A/en active Active
- GB GB1050733D patent/GB1050733A/en active Active
- GB GB1050740D patent/GB1050740A/en active Active
- GB GB1050735D patent/GB1050735A/en active Active
- GB GB1050734D patent/GB1050734A/en active Active
- GB GB1050732D patent/GB1050732A/en active Active
- GB GB1050737D patent/GB1050737A/en active Active
- GB GB1050739D patent/GB1050739A/en active Active
- GB GB1050731D patent/GB1050731A/en active Active
- GB GB1050730D patent/GB1050730A/en active Active
- GB GB1050738D patent/GB1050738A/en active Active
-
1964
- 1964-01-14 DE DE19641695492 patent/DE1695492A1/en active Pending
- 1964-01-24 DE DE19641770116 patent/DE1770116A1/en active Pending
- 1964-01-24 DE DE19641695488 patent/DE1695488A1/en active Pending
- 1964-01-24 DE DE19641770132 patent/DE1770132A1/en active Pending
- 1964-01-24 DE DE19641695490 patent/DE1695490A1/en active Pending
- 1964-01-24 DE DE19641695484 patent/DE1695484A1/en active Pending
- 1964-01-24 DE DE19641470059D patent/DE1470059B1/en active Pending
- 1964-01-24 DE DE19641695487 patent/DE1695487A1/en active Pending
- 1964-01-24 DE DE19641695485 patent/DE1695485A1/en active Pending
- 1964-01-24 DE DE19641695491 patent/DE1695491A1/en active Pending
- 1964-01-24 DE DE19641695486 patent/DE1695486A1/en active Pending
- 1964-01-24 DE DE19641793561 patent/DE1793561A1/en active Pending
- 1964-01-24 DE DE19641695489 patent/DE1695489A1/en active Pending
- 1964-01-24 DE DE19641770802 patent/DE1770802A1/en active Pending
- 1964-01-24 DE DE19641695493 patent/DE1695493A1/en active Pending
- 1964-01-24 DE DE19641770134 patent/DE1770134A1/en active Pending
- 1964-01-28 AT AT01821/67A patent/AT277992B/en not_active IP Right Cessation
- 1964-01-28 BR BR15647964A patent/BR6456479D0/en unknown
- 1964-01-29 FI FI16964A patent/FI46955C/en active
- 1964-01-31 CH CH236068A patent/CH457435A/en unknown
- 1964-01-31 CH CH236268A patent/CH557815A/en not_active IP Right Cessation
- 1964-01-31 CH CH1674768A patent/CH466290A/en unknown
- 1964-01-31 CH CH444166A patent/CH466285A/en unknown
- 1964-01-31 CH CH236168A patent/CH464202A/en unknown
- 1964-01-31 CH CH490268A patent/CH466286A/en unknown
- 1964-01-31 NL NL6400813A patent/NL6400813A/xx unknown
- 1964-01-31 CH CH1674468A patent/CH466288A/en unknown
- 1964-01-31 FR FR1559559D patent/FR1559559A/fr not_active Expired
- 1964-01-31 SE SE89267A patent/SE302463B/xx unknown
- 1964-01-31 SE SE88967A patent/SE317975B/xx unknown
- 1964-01-31 CH CH236368A patent/CH457436A/en unknown
- 1964-01-31 BE BE643268D patent/BE643268A/xx unknown
- 1964-01-31 DK DK598765A patent/DK109334C/en active
- 1964-01-31 CH CH236568A patent/CH464203A/en unknown
- 1964-01-31 CH CH235868A patent/CH457434A/en unknown
- 1964-01-31 CH CH490368A patent/CH466287A/en unknown
- 1964-01-31 CH CH1674568A patent/CH466289A/en unknown
- 1964-01-31 SE SE123764A patent/SE307948B/xx unknown
- 1964-01-31 DK DK598265A patent/DK109562C/en active
- 1964-01-31 DK DK598565A patent/DK109514C/en active
- 1964-01-31 CH CH419468A patent/CH466284A/en unknown
- 1964-01-31 CH CH236668A patent/CH457437A/en unknown
- 1964-01-31 DK DK48964A patent/DK112238B/en unknown
- 1964-01-31 CH CH236468A patent/CH466283A/en unknown
-
1965
- 1965-11-22 DK DK598965A patent/DK112314B/en unknown
- 1965-11-22 DK DK598665A patent/DK112239B/en unknown
- 1965-11-22 DK DK598365A patent/DK113501B/en unknown
- 1965-11-22 DK DK598465A patent/DK111751B/en unknown
- 1965-11-22 DK DK598865A patent/DK112313B/en unknown
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1966
- 1966-02-23 DK DK93366A patent/DK112447B/en unknown
- 1966-02-23 DK DK93266A patent/DK112446B/en unknown
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1967
- 1967-01-20 SE SE89367A patent/SE302133B/en unknown
- 1967-01-20 SE SE895/67A patent/SE320069B/xx unknown
- 1967-01-20 SE SE896/67A patent/SE320666B/xx unknown
- 1967-01-20 SE SE894/67A patent/SE320367B/xx unknown
- 1967-01-20 SE SE890/67A patent/SE307133B/xx unknown
- 1967-01-20 SE SE891/67A patent/SE304995B/xx unknown
- 1967-01-20 SE SE88667A patent/SE302130B/en unknown
- 1967-01-20 SE SE88867A patent/SE302132B/en unknown
- 1967-01-31 SE SE88767A patent/SE302131B/xx unknown
- 1967-02-23 CH CH115364A patent/CH489495A/en not_active IP Right Cessation
-
1970
- 1970-09-21 FI FI702570A patent/FI47097C/en active
- 1970-09-21 FI FI257570A patent/FI47101C/en active
- 1970-09-21 FI FI257070A patent/FI47097B/fi active
- 1970-09-21 FI FI257270A patent/FI47099C/en active
- 1970-09-21 FI FI257170A patent/FI47098C/en active
- 1970-09-21 FI FI257370A patent/FI47185C/en active
- 1970-09-21 FI FI257470A patent/FI47100C/en active
- 1970-09-21 FI FI256870A patent/FI47096C/en active
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